Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis
DOI: 10.1055/a-2655-3710
DOI: 10.1055/a-2655-3710
Short Review
Metallaphotoredox Reactions of Propargyl Alcohol Derivatives: New Perspectives on Allene Synthesis
Funding Information Financial support by the CNRS, the ICBMS, and the Université Claude Bernard Lyon 1 is acknowledged. TH thanks the Chinese Council Scholarship for a doctoral fellowship. AA thanks the Institut Universitaire de France (IUF) for its support.
Abstract
This short review provides an overview of the recent advances in the direct transformation of propargyl alcohol derivatives to allenes, benefiting from the merger of transition metal and photoredox catalytic systems. Two main strategies are discussed and organized around the mode of activation of the propargyl electrophile C–O bond, i.e., catalytic methods either involving oxidative addition or photoinduced homolytic cleavage as the key elementary steps.
Keywords
Propargyl alcohol derivatives - Metallaphotoredox catalysis - Allenes - C–O bond activation - Nickel catalysisPublication History
Received: 06 June 2025
Accepted after revision: 14 July 2025
Accepted Manuscript online:
14 July 2025
Article published online:
19 August 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Krause N, Hashmi ASK. Modern Allene Chemistry. Weinheim: Wiley-VCH; 2004
- 2 Ma S. Chem Rev 2005; 105: 2829
- 3 Hoffmann-Röder A, Krause N. Angew Chem Int Ed 2004; 43: 1196
- 4 Rivera-Fuentes P, Diederich F. Angew Chem Int Ed 2012; 51: 2818
- 5 Krause N, Hoffmann-Röder A. Tetrahedron 2004; 60: 11671
- 6 Yu S, Ma S. Chem Commun 2011; 47: 5384
- 7 Du S, Zhou A-X, Yang R, Song X-R, Xiao Q. Org Chem Front 2021; 8: 6760
- 8 Ma S. Eur J Org Chem 2004; 2004: 1175
- 9 O’Broin CQ, Guiry PJ. J Org Chem 2020; 85: 10321
- 10 Liu X, Jiao C, Cui S, Liu Q, Zhang X, Zhang G. ChemCatChem 2023; e202300601
- 11 Posevins D, Bäckvall J-E. J Organomet Chem 2022; 964: 122304
- 12 Ohmiya H, Yokobori U, Makida Y, Sawamura M. Org Lett 2011; 13: 6312
- 13 Vyas DJ, Hazra CK, Oestreich M. Org Lett 2011; 13: 4462
- 14 Li Y, Bao H. Chem Sci 2022; 13: 8491
- 15 Singh J, Saxena B, Sharma A. Catal Sci Technol 2024; 14: 5143
- 16 Xiao B-Y, Huang W, Zhang F-H. Eur J Org Chem. 2025
- 17 Chan AY, Perry IB, Bissonnette NB. et al. Chem Rev 2022; 122: 1485
- 18 Elsevier CJ, Kleijn H, Boersma J, Vermeer P. Organometallics 1986; 5: 716
- 19 Ogoshi S, Tsutsumi K, Kurosawa H. J Organomet Chem 1995; 493: C19
- 20 Baize MW, Blosser PW, Plantevin V, Schimpff DG, Gallucci JC, Wojcicki A. Organometallics 1996; 15: 164
- 21 Miyazaki Y, Michigami K, Ohashi M. J Am Chem Soc 2024; 146 (12) 8757
- 22 Ehehalt LE, Beleh OM, Priest IC. et al. Chem Rev 2024; 124: 13397
- 23 Crespi S, Fagnoni M. Chem Rev 2020; 120: 9790
- 24 Zhou Z-Z, Song X-R, Du S. et al. Chem Commun 2021; 57: 9390
- 25 Gutiérrez-Bonet A, Tellis JC, Matsui JK, Vara BA, Molander GA. ACS Catal 2016; 6: 8004
- 26 Zhou Z-Z, Zhai X-F, Xia K-J. et al. Org Chem Front 2024; 11: 5685
- 27 Yi J, Badir SO, Kammer LM, Ribagorda M, Molander GA. Org Lett 2019; 21: 3346
- 28 Crisenza GEM, Mazzarella D, Melchiorre P. J Am Chem Soc 2020; 142: 5461
- 29 Zhou Z-Z, Zhai X-F, Zhang S-L. et al. Org Chem Front 2023; 10: 298
- 30 Azpilcueta-Nicolas CR, Lumb J-P. Beilstein J Org Chem 2024; 20: 346
- 31 Hu T, Beluze C, Fagué V. et al. Org Lett 2024; 26: 9519
- 32 Julia F, Constantin T, Leonori D. Chem Rev 2022; 122: 2292
- 33 Beatty JW, Stephenson CRJ. Acc Chem Res 2015; 48: 1474
- 34 Nakajima K, Miyake Y, Nishibayashi Y. Acc Chem Res 1946; 2016: 49
- 35 Constantin T, Zanini M, Regni A, Sheikh NS, Juliá F, Leonori D. Science 2020; 367: 1021
- 36 Sachidanandan K, Niu B, Laulhé S. ChemCatChem 2023; 15: e202300860
- 37 Li M, Chia XL, Zhu Y. Chem Commun 2022; 58: 4719
- 38 Hu T, Fagué V, Bouyssi D, Monteiro N, Amgoune A. Green Chem 2024; 26: 6124
- 39 Tsuji J, Mandai T. Synthesis 1996; 1
- 40 Le C, Chen TQ, Liang T, Zhang P, MacMillan DWC. Science 2018; 360: 1010
- 41 Yu Y, Zhang J. Eur J Org Chem 2022; e202201017
- 42 Muresan M, Subramanian H, Sibi MP, Green JR. Eur J Org Chem 2021; 3359
- 43 Greaves PM, Landor SR, Laws DR. Chem Commun 1965; 321
- 44 Liu Q, Zheng J, Zhang X, Ma S. Nat Commun 2022; 13: 3302
- 45 Lu F-D, Shu Z-C, He G-F, Bai J-C, Lu L-Q, Xiao W-J. Org Chem Front 2022; 9: 5259
- 46 Shi S, Chen H, Yang S. et al. Org Lett 2024; 26: 7049
- 47 Chang L, An Q, Duan L, Feng K, Zuo Z. Chem Rev 2022; 122: 2429
- 48 Li W, Yu H, Ma S. Org Chem Front 2025; 12: 2401
- 49 Jarava-Barrera C, Parra A, Quesada S. et al. Adv Synth Catal 2024; 366: 768 and references cited therein
- 50 Yasui T, Yamada K, Tatsumi R, Yamamoto Y. ACS Catal 2021; 11: 11716